Terbinafine

Structural formula
General
Non-proprietary name	Terbinafine
other names	( E ) - N -6,6-trimethyl- N - (naphthalen-1-ylmethyl) hept-2-en-4-yn-1-amine ( IUPAC ) ( E ) - N - (6,6-Dimethyl-2-hepten-4-ynyl) - N -methyl-1-naphthylmethylamine
Molecular formula	C 21 H 25 N
External identifiers / databases
CAS number 91161-71-6 78628-80-5 (terbinafine hydrochloride ) PubChem 1549008 DrugBank DB00857 Wikidata Q415259
Drug information
ATC code	D01 AE15 D01 BA02
Drug class	Antifungal agent
properties
Molar mass	291.43 g · mol -1
Physical state	firmly
Melting point	195–198 ° C (terbinafine hydrochloride)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Hydrochloride Caution H and P phrases H: 315-319-335-410 P: 261-273-305 + 351 + 338-501
Toxicological data	4000 mg kg −1 ( LD 50 ,  rat ,  oral ) 4000 mg kg −1 ( LD 50 ,  mouse ,  oral ) 390 mg kg −1 ( LD 50 ,  mouse ,  iv )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Terbinafine is a drug that is used as an antifungal drug . This is an allylamine - derivative .

application

The active ingredient can be used topically or systemically and is mainly used externally to treat athlete's foot and internally to treat nail fungus (onychomycosis) and is a standard therapeutic agent for severe onychomycoses and dermatomycoses .

effect

Terbinafine inhibit ergosterol - synthesis in the fungal cell membrane. By inhibiting squalene epoxidase, terbinafine blocks the conversion of ( S ) -squalene-2,3-epoxide into lanosterol , the precursor of ergosterol. This results in an accumulation of squalene and an ergosterol deficiency in the cell membrane. In contrast to itraconazole , which blocks the conversion of lanosterol into ergosterol, terbinafine acts earlier in the synthesis path. Ultimately, however, both preparations block the formation of the cell membrane of fungi, for which ergosterol is an essential component.

Trade names

Monopreparations

Amiada (D), Amisan (A), Amykal (A), Dermatin (D), Fungizid-ratiopharm extra (D), Helvepidin (CH), Lamisil (D, A, CH), Mayfung (A), Myconormin (D , A, CH), Octosan (D), Pedibene (A), Tineafin (CH), Lamicosil (E), numerous generics (D, A, CH)

literature

• M. Haugh, S. Helou, JP Boissel, BJ Cribier: Terbinafine in fungal infections of the nails: a meta-analysis of randomized clinical trials. In: Br J Dermatol . 147, 2002, pp. 118-121.
• B. Sigurgeirsson, S. Billstein, T. Rantanen, T. Ruzicka, E. di Fonzo, BJ Vermeer, MJ Goodfield, EG Evans: LION. Study: efficacy and tolerability of continuous terbinafine (Lamisil) compared to intermittent itraconazole in the treatment of toenail onychomycosis. Lamisil vs. Itraconazole in Onychomycosis. In: Br J Dermatol. 141 Suppl, 56, 1999, pp. 5-14.
• MH. Schmid-Wendtner: Terbinafine: systemic and topical therapy of fungal infections. ABW-Verlag, Berlin 2006, ISBN 3-936072-44-2 .

Web links

• Entry on terbinafine in Pharmawiki
• Terbinafine ZTC
• Terbinafine tolerance (reading sample)

Individual evidence

1. ↑ ^{a b c d} Entry on terbinafine. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.
2. ↑ ^{a b} Data sheet Terbinafine hydrochloride from Sigma-Aldrich , accessed on October 23, 2016 ( PDF ).

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !